beta-Pedunculagin

Details

• Internal ID: c07c0a5e-301b-43c0-8bbd-3a773ee1531c
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: (1R,2S,19R,20R,22R)-7,8,9,12,13,14,20,28,29,30,33,34,35-tridecahydroxy-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.02,19.05,10.011,16.026,31.032,37]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaene-4,17,25,38-tetrone
• SMILES (Canonical): C1C2C(C3C(C(O2)O)OC(=O)C4=CC(=C(C(=C4C5=C(C(=C(C=C5C(=O)O3)O)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6C7=C(C(=C(C=C7C(=O)O1)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]2[C@H]([C@H]3[C@H]([C@@H](O2)O)OC(=O)C4=CC(=C(C(=C4C5=C(C(=C(C=C5C(=O)O3)O)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6C7=C(C(=C(C=C7C(=O)O1)O)O)O)O)O)O
• InChI: InChI=1S/C34H24O22/c35-10-1-6-15(23(43)19(10)39)16-7(2-11(36)20(40)24(16)44)31(48)54-27-14(5-52-30(6)47)53-34(51)29-28(27)55-32(49)8-3-12(37)21(41)25(45)17(8)18-9(33(50)56-29)4-13(38)22(42)26(18)46/h1-4,14,27-29,34-46,51H,5H2/t14-,27-,28+,29-,34-/m1/s1
• InChI Key: IYMHVUYNBVWXKH-MMQHQYPESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₂₄O₂₂
• Molecular Weight: 784.50 g/mol
• Exact Mass: 784.07592239 g/mol
• Topological Polar Surface Area (TPSA): 377.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.67
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 0

Synonyms

• VA85X55GDI
• UNII-VA85X55GDI
• 118014-30-5
• beta-D-Glucopyranose, cyclic 2,3:4,6-bis((1S)-4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylate)
• .BETA.-PEDUNCULAGIN
• Q27291724
• .BETA.-D-GLUCOPYRANOSE, CYCLIC 2,3:4,6-BIS((1S)-4,4',5,5',6,6'-HEXAHYDROXY(1,1'-BIPHENYL)-2,2'-DICARBOXYLATE)
• 4-O,6-O-[(4,4',5,5',6,6'-Hexahydroxy-1,1'-biphenyl-2,2'-diyl)biscarbonyl]-2-O,3-O-[(4,4',5,5',6,6'-hexahydroxy-1,1'-biphenyl-2,2'-diyl)biscarbonyl]-beta-D-glucopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5693	56.93%
Caco-2	-	0.8943	89.43%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5861	58.61%
OATP2B1 inhibitior	+	0.5787	57.87%
OATP1B1 inhibitior	+	0.8245	82.45%
OATP1B3 inhibitior	+	0.9673	96.73%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8528	85.28%
P-glycoprotein inhibitior	+	0.7201	72.01%
P-glycoprotein substrate	-	0.8841	88.41%
CYP3A4 substrate	+	0.5118	51.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8458	84.58%
CYP3A4 inhibition	-	0.8649	86.49%
CYP2C9 inhibition	-	0.7987	79.87%
CYP2C19 inhibition	-	0.9089	90.89%
CYP2D6 inhibition	-	0.9212	92.12%
CYP1A2 inhibition	-	0.8636	86.36%
CYP2C8 inhibition	-	0.8265	82.65%
CYP inhibitory promiscuity	-	0.9469	94.69%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7012	70.12%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8662	86.62%
Skin irritation	-	0.7337	73.37%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7795	77.95%
Micronuclear	+	0.7633	76.33%
Hepatotoxicity	-	0.5698	56.98%
skin sensitisation	-	0.8462	84.62%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6496	64.96%
Acute Oral Toxicity (c)	III	0.3250	32.50%
Estrogen receptor binding	+	0.7770	77.70%
Androgen receptor binding	+	0.6941	69.41%
Thyroid receptor binding	-	0.5171	51.71%
Glucocorticoid receptor binding	-	0.4637	46.37%
Aromatase binding	-	0.5596	55.96%
PPAR gamma	+	0.7000	70.00%
Honey bee toxicity	-	0.8535	85.35%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8783	87.83%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL244	P00742	Coagulation factor X	560 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.82%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.69%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.72%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.93%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.90%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.28%	94.00%
CHEMBL2581	P07339	Cathepsin D	84.96%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.41%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.26%	94.73%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.06%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.87%	100.00%
CHEMBL230	P35354	Cyclooxygenase-2	82.60%	89.63%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.51%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.82%	93.40%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.26%	90.71%

Plants that contains it

• Acacia sparsiflora
• Achyranthes bidentata
• Agave shawii
• Ambrosia grayi
• Astrantia major
• Camellia sasanqua
• Carpinus cordata
• Cassia javanica subsp. agnes
• Clusia multiflora
• Convallaria keiskei
• Davallia divaricata
• Dirca occidentalis
• Drypetes littoralis
• Edgeworthia gardneri
• Eucalyptus regnans
• Euphorbia iberica
• Grindelia hirsutula
• Hopea jucunda
• Juglans regia
• Khaya grandifoliola
• Kunzea ambigua
• Paeonia lactiflora
• Platycarya strobilacea
• Plumbago pulchella
• Plumeria alba
• Polygala ruwenzoriensis
• Quercus coccifera
• Rhodomyrtus tomentosa
• Rhoiptelea chiliantha
• Rumex conglomeratus
• Senecio glaucus subsp. coronopifolius
• Senegalia pennata
• Silene vulgaris
• Syzygium jambos
• Tainia latifolia
• Thesium humile
• Tilia europaea
• Xenophyllum decorum

Cross-Links

• PubChem: 5320441
• NPASS: NPC200684
• LOTUS: LTS0092963
• wikiData: Q27291724